Anthracene-based compound and organic light emitting device employing the same

ABSTRACT

Provided are an anthracene-based compound represented by Formula 1 or 2 and an organic light emitting device employing the same: 
     
       
         
         
             
             
         
       
     
     where R is a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C5-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aralkyl group or a substituted or unsubstituted C2-C30 heteroaryl group, L is a bivalent linking group and a substituted or unsubstituted C6-C30 arylene group or a substituted or unsubstituted C2-C30 heteroarylene group, and m is an integer of 0 to 3.

CROSS-REFERENCE TO RELATED PATENT APPLICATION AND CLAIM OF PRIORITY

This application claims the benefit of Korean Patent Application Nos.10-2007-0109731, filed on Oct. 30, 2007 and 10-2008-0039348, filed onApr. 28, 2008, in the Korean Intellectual Property Office, thedisclosure of which is incorporated herein in its entirety by reference.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention relates to an anthracene-based compound and anorganic light emitting device employing the same, and more particularly,to an anthracene-based compound including a pyridinylquinoline-basedgroup or a pyridinylisoquinoline-based group and an organic lightemitting device including an organic layer formed of theanthracene-based compound.

2. Description of the Related Art

Organic light emitting devices are active light emitting display devicesthat emit light by recombination of electrons and holes in a thin layermade of a fluorescent or phosphorescent organic compound (an organiclayer) when a current is applied to the organic layer. The organic lightemitting devices have advantages such as lightweight, simpleconstitutional elements, an easy fabrication process, superior imagequality and a wide viewing angle. Furthermore, the organic lightemitting devices can accomplish perfect creation of dynamic images andhigh color purity. The organic light emitting devices also haveelectrical properties, such as low power consumption and low drivingvoltage, suitable for portable electronic equipment

A multi-layered organic light emitting device using an aluminumquinolinol complex layer and a triphenylamine derivative layer wasdeveloped by Eastman Kodak Co. (U.S. Pat. No. 4,885,211), and a widerange of light from ultraviolet lights to infrared lights can be emittedusing low-molecular weight materials when an organic emitting layer isformed (U.S. Pat. No. 5,151,629).

Light emitting devices, which are self light emitting display devices,have wide viewing angles, excellent contrast and a quick response. Lightemitting devices are classified into inorganic light emitting devicesusing inorganic compounds to form emitting layers and organic lightemitting devices (OLED) using organic compounds to form emitting layers.Organic light emitting devices have higher brightness, lower drivingvoltages and quicker responses than inorganic light emitting devices andcan realize multi colors. Thus, organic light emitting devices have beenactively studied.

Typically, an organic light emitting device has an anode/organicemitting layer/cathode structure. An organic light emitting device canalso have various other structures, such as an anode/hole injectionlayer/hole transport layer/emitting layer/electron transportlayer/electron injection layer/cathode structure or an anode/holeinjection layer/hole transport layer/emitting layer/hole blockinglayer/electron transport layer/electron injection layer/cathodestructure.

Materials that are used in organic light emitting devices can beclassified into vacuum deposited materials and solution coated materialsaccording to a method of preparing an organic layer. The vacuumdeposited materials may have a vapor pressure of 10-⁶ torr or greater atthe temperature of 500° C. or less and may be low molecular materialshaving a molecular weight of 1200 or less. The solution coated materialsmay be highly soluble in solvents to be prepared in solution phase, andinclude aromatic or heterocyclic groups.

When an organic light emitting device is manufactured by vacuumdeposition, costs may be increased due to expensive vacuum systems andhigh resolution pixels may not be easily manufactured if a shadow maskis used to prepare pixels for a natural color display. On the otherhand, an organic light emitting device can be easily and inexpensivelymanufactured using solution coating such as inkjet printing, screenprinting and spin coating and can have relatively high resolutioncompared to when using a shadow mask.

Meanwhile, when a conventional organic light emitting device is operatedor stored at a high temperature, emitting light may be changed, lightemitting efficiency may be reduced, driving voltages may be increased,and lifetime may be shortened. In order to prevent those problems, anovel electron transport material having a high glass transitiontemperature (Tg) and capable of reducing driving voltage needs to bedeveloped.

Oxadiazole derivatives, triazole derivatives, phenanthroline derivativesand aluminum complexes are widely used as an electron transportmaterial. In particular, research on an electron transport materialusing a phenanthroline-based or bipyridine-based compound is vigorouslyperformed.

International Publication No. WO2007/026847 discloses a compound havinga triazole ring structure substituted with a pyridyl group, and JapanesePatent Publication No. hei 15-123983 discloses a1,10-phenanthroline-based compound to manufacture organic light emittingdevices having low driving voltage and high efficiency by using higherelectron transporting capability compared to conventional electrontransport materials.

SUMMARY OF THE INVENTION

According to an aspect of the present invention, there is provided ananthracene-based compound comprising a compound represented by Formula 1or 2 below:

wherein R is selected from the group consisting of a hydrogen atom, ahalogen atom, a cyano group, a hydroxyl group, a substituted orunsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20cycloalkyl group, a substituted or unsubstituted C5-C30 heterocycloalkylgroup, a substituted or unsubstituted C1-C20 alkoxy group, a substitutedor unsubstituted C6-C30 aryl group, a substituted or unsubstitutedC6-C30 aralkyl group and a substituted or unsubstituted C2-C30heteroaryl group,

L is a bivalent linking group and a substituted or unsubstituted C6-C30arylene group or a substituted or unsubstituted C2-C30 heteroarylenegroup, and

m is an integer of 0 to 3.

According to another aspect of the present invention, there is providedan organic light emitting device comprising:

a first electrode;

a second electrode; and

at least one organic layer between the first electrode and the secondelectrode, wherein the organic layer comprises the anthracene-basedcompound.

BRIEF DESCRIPTION OF THE DRAWINGS

A more complete appreciation of the present invention, and many of theabove and other features and advantages of the present invention, willbe readily apparent as the same becomes better understood by referenceto the following detailed description when considered in conjunctionwith the accompanying drawings in which like reference symbols indicatethe same or similar components, wherein:

FIG. 1A is a schematic sectional view of an organic light emittingdevice according to an embodiment of the present invention;

FIG. 1B is a schematic sectional view of an organic light emittingdevice according to another embodiment of the present invention;

FIG. 2A is a graph illustrating liquid chromatography-mass spectrometry(LCMS) results of a compound prepared according to Example 3;

FIG. 2B is a graph illustrating thermogravimetric analysis (TGA) resultsof a compound prepared according to Example 3;

FIG. 2C is a graph illustrating differential scanning calorimetry (DSC)of a compound prepared according to Example 3;

FIG. 3A is a graph illustrating current density-voltage characteristicsof the organic light emitting devices prepared according to Example 12and Comparative Example 1; and

FIG. 3B is a graph illustrating voltage-brightness characteristics ofthe organic light emitting device prepared according to Example 12 andComparative Example 1.

DETAILED DESCRIPTION OF THE INVENTION

Hereinafter, the present invention will now be described more fully withreference to the accompanying drawings, in which exemplary embodimentsof the invention are shown.

According to an embodiment of the present invention, an anthracene-basedcompound represented by Formula 1 or 2, i.e., anthracene having apyridinylquinoline-based group or a pyridinylisoquinoline-based group.

In Formula 1 or 2, R is a hydrogen atom, a halogen atom, a cyano group,a hydroxyl group, a substituted or unsubstituted C1-C20 alkyl group, asubstituted or unsubstituted C3-C20 cycloalkyl group, a substituted orunsubstituted C5-C30 heterocycloalkyl group, a substituted orunsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30aryl group, a substituted or unsubstituted C6-C30 aralkyl group or asubstituted or unsubstituted C2-C30 heteroaryl group;

L is a bivalent linking group and a substituted or unsubstituted C6-C30arylene group or a substituted or unsubstituted C2-C30 heteroarylenegroup; and

m is 0, 1, 2 or 3.

In Formula 1 or 2, a hydrogen atom of the “Anthracene” is substitutedwith the pyridinylquinoline-based group or thepyridinylisoquinoline-based group, and the other hydrogens of the“Anthracene” may be substituted or unsubstituted.

Here, the position of the carbons of anthracene is numbered as follows.

In the anthracene-based compound according to an embodiment of thepresent invention, the hydrogen of the “Anthracene” in Formula 1 or 2may be substituted with the pyridinylquinoline-based group or thepyridinylisoquinoline-based group in one of the positions selected fromthe group consisting of C2, C3, C6, C7, C9 and C10 positions ofanthracene.

The anthracene-based compound may be represented by one of Formulae 3 to6 below:

wherein R₁ to R₁₇ are identical to or different from each other and eachindependently one selected from the group consisting of a hydrogen atom,a halogen atom, a cyano group, a hydroxyl group, a substituted orunsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20cycloalkyl group, a substituted or unsubstituted C5-C30 heterocycloalkylgroup, a substituted or unsubstituted C1-C20 alkoxy group, a substitutedor unsubstituted C6-C30 aryl group, a substituted or unsubstitutedC6-C30 aralkyl group and a substituted or unsubstituted C2-C30heteroaryl group;

Ar₁l, Ar₂ and Ar₃ are identical to or different from each other and areeach independently a substituted or unsubstituted C6-C30 aryl group;

L is a bivalent linking group, and L is a substituted or unsubstitutedC6-C30 arylene group or a substituted or unsubstituted C2-C30heteroarylene group; and

m is 0, 1, 2 or 3.

For example, in Formulae 3 to 6, L is independently one of the bivalentlinking group and may be represented by formulae A-1 through A-21 below:

wherein R′ is identical to or different from each other and one selectedfrom the group consisting of a hydrogen atom, a halogen atom, a cyanogroup, a hydroxyl group, a substituted or unsubstituted C1-C20 alkylgroup, a substituted or unsubstituted C3-C20 cycloalkyl group, asubstituted or unsubstituted C5-C30 heterocycloalkyl group, asubstituted or unsubstituted C1-C20 alkoxy group, a substituted orunsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30aralkyl group and a substituted or unsubstituted C2-C30 heteroarylgroup.

In Formulae 3 to 6, Ar₁, Ar₂ and Ar₃ are identical to or different fromeach other, and each independently represented by any one of theformulae B1 through B-17 below:

wherein R′ is identical to or different from each other and one selectedfrom the group consisting of a hydrogen atom, a halogen atom, a cyanogroup, a hydroxyl group, a substituted or unsubstituted C1-C20 alkylgroup, a substituted or unsubstituted C3-C20 cycloalkyl group, asubstituted or unsubstituted C5-C30 heterocycloalkyl group, asubstituted or unsubstituted C1-C20 alkoxy group, a substituted orunsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30aralkyl group and a substituted or unsubstituted C2-C30 heteroarylgroup.

The alkyl group used herein as a substituent may be a linear or branchedalkyl group having 1 to 20 carbon atoms, preferably 1 to 12 carbonatoms, and more preferably 1 to 6 carbon atoms. Examples of theunsubstituted alkyl group are a methyl group, an ethyl group, ann-propyl group, an isopropyl group, a n-butyl group, an isobutyl group,a sec-butyl group, a t-butyl group, a pentyl group, an iso-amyl groupand a hexyl group.

The cycloalkyl group used herein is a monovalent monocyclic systemhaving 3 to 20 carbon atoms, preferably 3 to 10 carbon atoms, and morepreferably 3 to 6 carbon atoms.

The heterocycloalkyl group used herein is a monovalent monocyclic systemhaving 3 to 20 carbon atoms, preferably 3 to 10 carbon atoms, and morepreferably 3 to 6 carbon atoms, 1, 2 or 3 carbon atoms of which aresubstituted with N, O, P and S.

The alkoxy group used herein as a substituent may be anoxygen-containing linear or branched alkoxy group having an alkyl moietyconsisting of 1 to 20 carbon atoms, preferably 1 to 6 carbon atoms, andmore preferably 1 to 3 carbon atoms. Examples of the alkoxy group are amethoxy group, an ethoxy group, a propoxy group, a butoxy group and at-butoxy group. Such an alkoxy group can further be substituted by atleast one halo atom such as fluoro, chloro and bromo to provide ahaloalkoxy group. Examples of the haloalkoxy group are a fluoromethoxygroup, a chloromethoxy group, a trifluoromethoxy group, atrifluoroethoxy group, a fluoroethoxy group and a fluoropropoxy group.

The aryl group as a substituent is used alone or in a combination, andis a carbocyclic aromatic system having 6 to 30 carbon atoms and one ormore rings. The rings may be attached using a pendent manner or fusedtogether. The term “aryl” includes aromatic radicals such as phenyl,naphthyl, tetrahydronaphthyl, indane and biphenyl. For example, the arylgroup may be phenyl.

The aralkyl used herein is an alkyl group in which at leas one hydrogenatom is substituted with the aryl group.

The heteroaryl group used herein as a substituent is a monovalentmonocyclic or bicyclic aromatic radical having at least one 5 to 30membered ring(s) in which one, two or three atoms are N, O or S. Theheteroaryl group may be a monovalent monocyclic or bicyclic aromaticradical in which the hetero atoms is oxidized or quaternized to form,for example, an N-oxide or a quaternary salt. Examples of the heteroarylgroup are thienyl, benzothienyl, pyridyl, pyrazinyl, pyrimidinyl,pyridazinyl, quinolinyl, quinoxalinyl, imidazolyl, furanyl,benzofuranyl, thiazolyl, isoxazolyl, benzisoxazolyl, benzimidazolyl,triazolyl, pyrazolyl, pyrolyl, indolyl, 2-pyridonyl,N-alkyl-2-pyridonyl, pyrazinonyl, pyridazynonyl, pyrimidinonyl,oxazolonyl, corresponding N-oxides thereof (e.g., pyridyl N-oxide andquinolinyl N-oxide), and quaternary salts thereof, but are not limitedthereto.

When the alkyl group, the alkoxy group, the aryl group, the heteroarylgroup, the cycloalkyl group and the heterocycloalkyl group aresubstituted, the substituents may be at least one of —F; —Cl; —Br; —CN;—NO₂; —OH; a C1-C20alkyl group that is unsubstituted or substituted with—F, —Cl, —Br, —CN, —NO₂ or —OH; a C1-C20 alkoxy group that isunsubstituted or substituted with —F, —Cl, —Br, —CN, —NO₂ or —OH; aC6-C30 aryl group that is unsubstituted or substituted with a C1-C20alkyl group, a C1-C20 alkoxy group, —F, —Cl, —Br, —CN, —NO₂ or —OH; aC2-C30 heteroaryl group that is unsubstituted or substituted with aC1-C20 alkyl group, a C1-C20 alkoxy group, —F, —Cl, —Br, —CN, —NO₂ or—OH; a C5-C20 cycloalkyl group that is unsubstituted or substituted witha C1-C20 alkyl group, a C1-C20 alkoxy group, —F, —Cl, —Br, —CN, —NO₂ or—OH; a C5-C30 heterocycloalkyl group that is unsubstituted orsubstituted with a C1-C20 alkyl group, a C1-C20 alkoxy group, —F, —Cl,—Br, —CN, —NO₂ or —OH; and —N(G6)(G7). Here, G6 and G7 are eachindependently a hydrogen atom; C1-C1 alkyl group; or a C6-C30 aryl groupsubstituted with a C1-C10 alkyl group.

In particular, R₁ to R₁₇ are each independently selected from the groupconsisting of a hydrogen atom, a halogen atom, a cyano group, a hydroxylgroup, a C1-C10 alkyl group, a C1-C10 alkoxy group and a substituted orunsubstituted derivative such as: a phenyl group, a biphenyl group, apentalenyl group, an indenyl group, a naphthyl group, a biphenylenylgroup, an anthracenyl group, an azulenyl group, a heptalenyl group, anacenaphthylenyl group, a phenalenyl group, a fluorenyl group, amethylanthryl group, a phenanthrenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, an ethyl-chrysenyl group, a picenylgroup, a perylenyl group, a chloroperylenyl group, a pentaphenyl group,a pentacenyl group, a tetraphenylenyl group, a hexaphenyl group, ahexacenyl group, a rubicenyl group, a coronenyl group, a trinaphthylenylgroup, a heptaphenyl group, a heptacenyl group, a fluorenyl group, apyranthrenyl group, an ovalenyl group, a carbazolyl group, a thiophenylgroup, an indolyl group, a purinyl group, a benzimidazolyl group, aquinolinyl group, a benzothiophenyl group, a parathiazinyl group, apyrrolyl group, a pyrazolyl group, an imidazolyl group, an imidazolinylgroup, an oxazolyl group, a thiazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a pyridinyl group, a pyridazinylgroup, a pyrimidinyl group, a pyrazinyl group, a thianthrenyl group, acyclopentyl group, a cyclohexyl group, an oxiranyl group, a pyrrolidinylgroup, a pyrazolidinyl group, an imidazolidinyl group, a piperidinylgroup, a piperazinyl group, a morpholinyl group, a di(C6-C30 aryl)aminogroup, a tri(C6-C30 aryl)silyl group and derivatives thereof.

Here, the term “derivative” indicates the above-listed group in which atleast one of the hydrogen atoms is substituted with the substituentsdescribed above.

The anthracene-based compound according to an embodiment of the presentinvention has high solubility in a solvent in the formation of anorganic layer, high thermal stability since a glass transitiontemperature (Tg) is high due to a delocalized electron distribution anda rigid structure, and excellent electron injecting and transportingcapability since the pyridinylquinoline-based compound or thepyridinylisoquinoline-based compound is introduced thereinto. Thus, anorganic light emitting device employing the anthracene-based compoundcan have low driving voltage and high efficiency.

The compound according to an embodiment of the present invention may berepresented by one of Formulae 7 to 50 below, but is not limitedthereto.

The compound according to an embodiment of the present invention may besynthesized using a synthesis principle that is commonly used in theart. A synthetic pathway of the compound is described with respect tosynthesis examples.

An organic light emitting device according to an embodiment of thepresent invention may include a first electrode; a second electrode; andan organic layer interposed between the first electrode and the secondelectrode, wherein the organic layer includes at least oneanthracene-based compound having a compound represented by Formula 1 or2.

The anthracene-based compound is suitably used to form an organic layer,preferably an emitting layer, an electron injection layer, an electrontransport layer or a hole blocking layer. An emitting layer of theorganic light emitting device of an embodiment of the present inventionmay include a phosphorescent or fluorescent dopant for red, green, blueor white color. The phosphorescent dopant may be an organic metalcompound including at least one element selected from the groupconsisting of Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb and Tm.

The organic light emitting device of an embodiment of the presentinvention has improved emitting properties such as low driving voltageand high color purity by employing a compound having high solubility andthermal stability and capable of forming a stable organic layer whencompared to a conventional organic light emitting device prepared usinga solution coating method and having low stability of organic layer.

The organic light emitting device of an embodiment of the presentinvention may have various structures. That is, the organic lightemitting device may further include at least one layer selected from thegroup consisting of a hole injection layer, a hole transport layer, ahole blocking layer, an electron blocking layer, an electron transportlayer and an electron injection layer between the first electrode andthe second electrode.

More particularly, FIGS. 1A and 1B are schematic sectional views oforganic light emitting devices according to embodiments of the presentinvention. The organic light emitting device of FIG. 1A has a structureof a first electrode/a hole injection layer/a hole transport layer/anemitting layer/an electron transport layer/an electron injection layer/asecond electrode. The organic light emitting device of FIG. 1B has astructure of a first electrode/a hole injection layer/an emittinglayer/an electron transport layer/an electron injection layer/a secondelectrode.

The organic layer in the organic light emitting device according to anembodiment of the present invention may further include an organic metalcomplex.

The organic metal complex is a compound having an organic ligandconnected to a metal only by coordinate bonds.

Here, the metal may be an alkali metal (I) such as Li, Na, K, Rb and Cs;an alkaline earth metal (II) such as Mg, Ca, Sr and Ba; and a rare earthmetal (III) such as Y, La, Ce, Pr, Nd, Sm, Eu, Er and Yb.

The ligands coordinated to the metal in the organic metal complex may beβ-diketones such as acetyl acetone, 1,3-diphenyl-1,3-propanedioene,2,2,6,6-tetramethyl-3,5-hepanedione,1,1,1,2,2,3,3,-heptafluoro-7,7-dimethyl-4,6-octanedione and1-phenyl-1,3-butanedione, salicyl aldehydes such as salicyl aldehyde anddiethylaminosalicyl aldehyde, anthracene, naphthalene, phenanthrene,pyrene, tetracene, coronene, chrysene, fluorescein, perylene,phthaloperylene, naphthaloperylene, perinone, phthaloperinone,naphthaloperinone, diphenylbutadiene, tetraphenylbutadiene, coumarin,oxadiazole, aldazine, bisbenzoxazoline, bistyryl, pyrazine,cyclopentadiene, quinoline, aminoquinoline, benzoquinoline, or the like.

The amount of the organic metal complex may be in the range of 0.01 to90 parts by weight, and preferably 0.1 to 60 parts by weight, based on100 parts by weight of a solid that is used to form an organic layer.When the amount of the organic metal complex is less than 0.01 parts byweight, emitting efficiency is not sufficiently improved and electroninjection effect is not sufficient. On the other hand, when the amountof the organic metal complex is more than 90 parts by weight, electrontransporting capability may be decreased.

The organic layer in the organic light emitting device according to anembodiment of the present invention may further include an ionic saltsuch as an inorganic salt, an organic salt or a metal salt.

Examples of the ionic salt in the organic layer are: a Li-containinginorganic salt such as LiClO₄, LiPF₆, LiBF₄, LiN(CF₃SO₂)₂ and lithiumtrifluoromethane sulfonate; an organic salt such as tetraethylammoniumtetrafluoroborate (TEA-BF₄), tetra-n-butylammonium tetrafluoroborate(Bu₄N—BF₄), tetraalkyl, aryl or heteroaryl quaternary ammonium salt suchas tetra-n-alkylammonium toluenesulfonate, tetra-n-alkylammoniumtetrafluoroborate, tetra-n-alkyl ammonium tetraphenylborate,tetra-n-alkyl ammonium toluenesulfonate, tetraalkylammonium tetrafluoroborate and tetra-n-alkyl ammonium tetraphenylborate; and a polymericsalt such as polystyrenesulfonate (PSS).

Examples of the metal salt have a metal such as Al (III), Mn (II), Zr(IV), Ti (II), Hf (IV), Ta (V), Nb (III) and V (II). The inorganic saltis prepared by substituting hydrogen atoms of an inorganic acid, andexamples of the inorganic salt are a halide such as chloride, fluoride,bromide and iodide. The organic metal salt is prepared by substitutinghydrogen atoms of an organic acid, an alcohol and a dialkylamide, andexamples of the organic salt are: an organic acid salt such ascarboxylic acid and phenol; and salts of alkoxides and dialkylamides.

Here, the carboxylic acid may be aliphatic or aromatic. The aliphaticcarboxylic acid may have 1 to 24 carbon atoms, and may be a saturated orunsaturated aliphatic carboxylic acid. The aliphatic carboxylic acid mayhave one or more carboxyl groups or optionally a substituent such as anaryl group. Examples of the aliphatic carboxylic acid are a saturatedaliphatic carboxylic acid such as acetic acid, propionic acid, octylacid, iso-octyl acid, decanoic acid, lauric acid; an unsaturatedaliphatic carboxylic acid such as oleic acid and ricinoleic acid; and apolyhydric (di or tri) carboxylic acid such as citric acid and oxalicacid. The aromatic carboxylic acid may have 7 to 24 carbon atoms and asubstituent such as a C1-C8 alkyl group and a hydroxyl group. Examplesof the aromatic carboxylic acid are benzoic acid, o-(t-butyl)benzoicacid, m-(t-butyl)benzoic acid, salicylic acid, m-(hydroxy)benzoic acidand p-(hydroxy)benzoic acid). The phenol may have 6 to 46 carbon atoms,a substituent such as a C1-C8 linear or branched alkyl group, a phenylgroup and an aryl group, and a condensed ring, for example, an aromaticring such as a benzene ring having a substituent ring. The phenol groupmay be a monovalent phenol or a polyvalent phenol. Examples of thephenol are phenol, naphthol, 4-phenylphenol and2,2-bis(p-hydroxyphenyl)propane (bisphenol A). The alcohol formingalkoxide may have 1 to 10 carbon atoms, and examples are: a primaryalcohol such as ethyl alcohol, n-propyl alcohol and n-butyl alcohol; asecondary alcohol such as isopropyl alcohol and s-butyl alcohol; atertiary alcohol such as t-butyl alcohol; and a polyhydric alcohol suchas ethylene glycol.

The dialkylamide salt may have a substituent and 2 to 24 carbon atoms.Examples of the dialkylamide salt are dimethylamide, diethylamide andN-methyl-N-ethylamide.

However, the listed salts are examples of ionic salts which can be usedin the present invention, and any salts having cations and anions can beused herein.

The amount of the ionic salt may vary according to the use, element andthickness of an emitting layer. The amount of the ionic salt, however,may be in the range of 0.01 to 50 parts by weight, and preferably 1 to30 parts by weight based on 100 parts by weight a solid that is used toform an organic layer. Here, when the amount of the ionic salt is lessthan 0.01 parts by weight, emitting efficiency of the organic lightemitting device may not be sufficiently improved and break-down voltagemay not be sufficiently reduced. On the other hand, when the amount ofthe ionic salt is more than 50 parts by weight, the organic lightemitting device may not be properly operated due to excess concentrationof ions.

Hereinafter, a method of preparing an organic light emitting deviceaccording to an embodiment of the present invention will be describedwith reference to FIG. 1A.

First, a first electrode is formed on a substrate, for example, bydepositing or sputtering a high work-function material. The firstelectrode can be an anode. The substrate, which can be any substratethat is used in conventional organic light emitting devices, may be aglass substrate or a transparent plastic substrate with excellentmechanical strength, thermal stability, transparency, surfacesmoothness, ease of treatment, and waterproof. The material that is usedto form the first electrode can be ITO, IZO, SnO₂, ZnO, or anytransparent material which has high conductivity.

Then, a hole injection layer (HIL) can be formed on the first electrodeby vacuum deposition, spin coating, casting, langmuir Blodgett (LB), orthe like.

When the hole injection layer is formed by vacuum deposition, depositionconditions may vary according to a compound that is used to form thehole injection layer, and the structure and thermal properties of thehole injection layer to be formed. In general, however, conditions forvacuum deposition may include a deposition temperature of 100 to 500°C., a pressure of 10⁻⁸ torr to 10⁻³ torr, a deposition speed of 0.01 to100 Å/sec, and a layer thickness of 10 Å to 5 μm.

When the hole injection layer is formed by spin coating, coatingconditions may vary according to a compound that is used to form thehole injection layer, and the structure and thermal properties of thehole injection layer to be formed. In general, however, conditions forspin coating may include a coating speed of 2000 to 5000 rpm and aheat-treatment temperature of about 80 to 200° C. to remove a solventafter coating.

The thickness of the HIL may be in the range of about 100 to 10000 Å,and preferably in the range of 100 to 1000 Å. When the thickness of theHIL is less than 100 Å, the hole injecting ability of the HIL may bereduced. On the other hand, when the thickness of the HIL is greaterthan 10000 Å, a driving voltage of the device may be increased.

Then, a hole transport layer (HTL) can be formed on the HIL by vacuumdeposition, spin coating, casting, LB, or the like. When the HTL isformed by vacuum deposition or spin coating, the conditions fordeposition and coating are similar to those for the formation of theHIL, although conditions for the deposition and coating may varyaccording to the material that is used to form the HTL.

The thickness of the HTL may be in the range of about 50 to 1000 Å, andpreferably 100 to 600 Å. When the thickness of the HTL is less than 50Å, a hole transporting ability of the HTL may be reduced. On the otherhand, when the thickness of the HTL is greater than 1000 Å, the drivingvoltage of the device may be increased.

Then, an emitting layer (EML) can be formed on the HTL by vacuumdeposition, spin coating, casting, LB, or the like. When the EML isformed by vacuum deposition or spin coating, the conditions fordeposition and coating are similar to those for the formation of theHIL, although the conditions for deposition and coating may varyaccording to the material that is used to form the EML.

The thickness of the EML may be in the range of about 100 to 1000 Å, andpreferably in the range of 200 to 600 Å. When the thickness of the EMLis less than 100 Å, the emitting ability of the EML may be reduced. Onthe other hand, when the thickness of the EML is greater than 1000 Å,the driving voltage of the device may be increased.

A hole blocking layer (HBL) can be formed on the HTL by vacuumdeposition, spin coating, casting, LB, or the like, to prevent diffusionof triplet excitons or holes into an electron transport layer when thephosphorescent dopant is used to form the EML. When the HBL is formed byvacuum deposition or spin coating, the conditions for deposition andcoating are similar to those for the formation of the HIL, although theconditions for deposition and coating may vary according to the materialthat is used to form the HBL. The HBL may be formed of a compoundrepresented by one of Formulae 3 to 6, an oxadiazole derivative, atriazole derivative, a phenanthroline derivative, BCP or an aluminumcomplex.

The thickness of the HBL may be in the range of about 50 to 1000 Å, andpreferably in the range of 100 to 300 Å. When the thickness of the HBLis less than 50 A, the hole blocking ability of the HBL may be reduced.On the other hand, when the thickness of the HBL is greater than 1000 Å,the driving voltage of the device may be increased.

Then, an electron transport layer (ETL) is formed by vacuum deposition,spin coating, casting, or the like. When the ETL is formed by vacuumdeposition or spin coating, the conditions for deposition and coatingare, in general, similar to those for the formation of the HIL, althoughthe conditions for the deposition and coating conditions may varyaccording to the material that is used to form the ETL. The ETL may beformed of a known material in the art which stably transports injectedelectrons from a cathode, for example, a compound represented by one ofFormulae 3 to 6, an oxazole-based compound, an iso-oxazole-basedcompound, a triazole-based compound, an isothiazole-based compound, anoxadiazole-based compound, a thiadiazole-based compound, aperylene-based compound, an aluminum complex such astris(8-quinolinolato)-aluminium (Alq3), BAlq, SAlq, Almq3, a galliumcomplex such as Gaq′2OPiv, Gaq′2OAc and 2(Gaq′2), or the like.

The thickness of the ETL may be in the range of about 100 to 1000 Å, andpreferably 200 to 500 Å. When the thickness of the ETL is less than 100Å, the electron transporting ability of the ETL may be reduced. On theother hand, when the thickness of the ETL is greater than 1000 Å, thedriving voltage of the device may be increased.

Then, an electron injection layer (EIL), which is formed of a materialallowing easy injection of electrons from a cathode, can be formed onthe ETL. The material that is used to form the EIL is not limited.

The EIL may be formed of LiF, NaCI, CsF, Li₂O, BaO, or the like, whichis known in the art. Conditions for the deposition of the EIL are, ingeneral, similar to conditions for the formation of the HIL, althoughthey may vary according to the material that is used to form the EIL.

The thickness of the EIL may be in the range of about 1 to 100 Å, andpreferably 5 to 50 Å. When the thickness of the EIL is less than 1 Å,the electron injecting ability of the EIL may be reduced. On the otherhand, when the thickness of the EIL is greater than 100 Å, the drivingvoltage of the device may be increased.

Finally, a second electrode can be formed on the EIL by vacuumdeposition, sputtering, or the like. The second electrode can be used asa cathode. The second electrode may be formed of a low work-functionmetal, alloy, electrically conductive compound or a combination ofthese. In detail, the second electrode may be formed of Li, Mg, Al,Al—Li, Ca, Mg—In, Mg—Ag, or the like. Alternatively, a transparentcathode formed of ITO or IZO can be used to produce a top emission lightemitting device.

Hereinafter, the present invention will be described in greater detailwith reference to the following examples. The following examples are forillustrative purposes only and are not intended to limit the scope ofthe invention.

EXAMPLE 1 1) Synthesis of 3-(5-bromo-pyridin-3-yl)-quinoline

1.11 g (4.7 mmol) of 3,5-dibromo-pyridin, 1.0 g (3.92 mmol) of3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-quinoline, 0.45 g oftetrakis(triphenylphosphine)palladium(0), 7.84 ml of 2 M K₂CO₃ and 1.26g of tetrabutylammoniumbromide were added to a 100 ml round-bottom flaskin an argon atmosphere, and 30 ml of THF and 15 ml of toluene were addedthereto. Then, the mixture was refluxed at 100° C. for 16 hours. Whenthe mixture solution turned dark brown, water was added thereto and themixture was subject to extraction using chloroform. Then, an organiclayer extracted therefrom was dried using anhydrous magnesium sulfateand filtered. A solvent was removed and the resultant was separatedusing a silica gel column chromatography to obtain 1.1 g of white solid3-(5-bromo-pyridin-3-yl)-quinoline which was identified by anatmospheric pressure chemical ionization (APCI) using LCMS (SHIMADZU,LCMS-IT-TOF). As a result, a main peak was observed at [M+H]+=285.

2) Synthesis of a Compound Represented by Formula 9

0.61 g (2.15 mmol) of 3-(5-bromo-pyridin-3-yl)-quinoline, 1.0 g (1.8mmol) of2-(9,10-di-naphthalene-2-yl-anthracen-2-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane,3.6 ml of 1 M K₃PO₄ and 20 ml of dioxane were added to a 100 mlround-bottom flask in an argon atmosphere, and the mixture was refluxedat 120° C. for 36 hours. When the reaction is completed, the reactionsolution was cooled to room temperature, and 100 ml of toluene and 100ml of distilled water were added thereto to extract an organic layer.The collected organic layer was dried using MgSO₄ and concentrated. Theresultant was separated using a silica gel chromatography. Here, anelute solution obtained therefrom was concentrated and dried to obtain1.1 g of a solid compound represented by Formula 9 which was identifiedby APCI using LCMS. As a result, a main peak was observed at [M+H]+=635.

EXAMPLE 2 1) Synthesis of 3-(6-bromo-pyridin-3-yl)-quinoline

1.11 g (4.7 mmol) of 2,6-dibromo-pyridin, 1.0 g (3.92 mmol) of3-(4,4,5,5-tetramethyll-[1,3,2]dioxaborolan-2-yl)-quinoline, 0.45 g oftetrakis(triphenylphosphine)palladium(0), 7.84 ml of 2M K₂CO₃ and 1.26 gof tetrabutylammoniumbromide were added to a 100 ml round-bottom flaskin an argon atmosphere, and 30 ml of THF and 15 ml of toluene were addedthereto. Then, the mixture was refluxed at 100° C. for 16 hours. Whenthe mixture solution turned dark brown, water was added thereto and themixture was subject to extraction using chloroform. Then, an organiclayer extracted therefrom was dried using anhydrous magnesium sulfateand filtered. A solvent was removed and the resultant was separatedusing a silica gel column chromatography to obtain 0.8 g of white solid3-(6-bromo-pyridin-2-yl)-quinoline which was identified by APCI usingLCMS. As a result, a main peak was observed at [M+H]+=285.

2) Synthesis of a Compound Represented by Formula 10

0.6 g (2.15 mmol) of 3-(6-bromo-pyridin-2-yl)-quinoline, 1.0 g (1.8mmol) of2-(9,10-di-naphthalene-2-yl-anthracene-2-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolan,3.6 ml of 1 M K₃PO₄ and 20 ml of dioxane were added to a 100 mlround-bottom flask in an argon atmosphere, and the mixture was refluxedat 120° C. for 36 hours. When the reaction is completed, the reactionsolution was cooled to room temperature, and 100 ml of toluene and 100ml of distilled water were added thereto to extract an organic layer.The collected organic layer was dried using MgSO₄ and concentrated. Theresultant was separated using a silica gel chromatography. An elutesolution obtained therefrom was concentrated and dried to obtain 0.9 gof a compound represented by Formula 10 which was identified by APCIusing LCMS. As a result, a main peak was observed at [M+H]+=635.

EXAMPLE 3 1) Synthesis of 3-(5-bromo-pyridin-2-yl)-quinoline

1.1 g (4.7 mmol) of 2,5-dibromo-pyridin, 1.0 g (3.92 mmol) of3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-quinoline, 0.45 g oftetrakis(triphenylphosphine)palladium(0), 7.84 ml of 2M K₂CO₃ and 1.26 gof tetrabutylammoniumbromide were added to a 100 ml round-bottom flaskin an argon atmosphere, and 30 ml of THF and 15 ml of toluene were addedthereto. Then, the mixture was refluxed at 100° C. for 16 hours. Whenthe mixture solution turned dark brown, water was added thereto and themixture was subject to extraction using chloroform. Then, an organiclayer extracted therefrom was dried using anhydrous magnesium sulfateand filtered. A solvent was removed and the resultant was separatedusing a silica gel column chromatography to obtain 1.2 g of white solid3-(5-bromo-pyridin-2-yl)-quinoline which was identified by APCI usingLCMS. As a result, a main peak was observed at [M+H]+=285.

2) Synthesis of a Compound Represented by Formula 11

0.62 g (2.15 mmol) of 3-(5-bromo-pyridin-2-yl)-quinoline, 1.0 g (1.8mmol) of2-(9,10-di-naphthalene-2-yl-anthracene-2-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolan,3.6 ml of 1 M K₃PO₄ and 20 ml of dioxane were added to a 100 mlround-bottom flask in an argon atmosphere, and the mixture was refluxedat 120° C. for 36 hours. When the reaction is completed, the reactionsolution was cooled to room temperature, and 100 ml of toluene and 100ml of distilled water were added thereto to extract an organic layer.The collected organic layer was dried using MgSO₄ and concentrated. Theresultant was separated using a silica gel chromatography. An elutesolution obtained therefrom was concentrated and dried to obtain 1.1 gof a compound represented by Formula 11 which was identified by APCIusing LCMS. As a result, a main peak was observed at [M+H]+=635.

FIG. 2A is a graph illustrating LCMS results of a compound preparedaccording to Example 3. In addition, thermal analysis of the compound ofFormula 11 was performed using a thermo gravimetric analysis (TGA) in aN₂ atmosphere at a temperature in the range of room temperature to 600°C. at 10° C./min in a Pt pan in a disposable Al pan and a differentialscanning calorimetry (DSC) at a temperature in the range of roomtemperature to 400° C. in a disposable Al pan. As a result, Td was 467°C. and Tg was 163° C. FIG. 2B is a graph illustrating thermogravimetricanalysis (TGA) results of the compound of Formula 11 prepared accordingto Example 3 and FIG. 2C is a graph illustrating differential scanningcalorimetry (DSC) of the compound of Formula 11 prepared according toExample 3.

EXAMPLE 4 1) Synthesis of 4-(5-bromo-pyridin-2-yl)-isoquinoline

4-(5-bromo-pyridin-2-yl)-isoquinoline was synthesized in the same manneras in Example 1-1), except that 2,5-dibromo-pyridin was used instead of3,5-dibromo-pyridin and4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-isoquinoline was usedinstead of 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-quinoline.The 4-(5-bromo-pyridin-2-yl)-isoquinoline was identified by APCI usingLCMS. As a result, a main peak was observed at [M+H]+=285.

2) Synthesis of a Compound Represented by Formula 12

A compound represented by Formula 12 was synthesized in the same manneras in Example 1-2), except that 4-(5-bromo-pyridin-2-yl)-isoquinolinewas used instead of 3-(5-bromo-pyridin-3-yl)-quinoline. The compound ofFormula 12 was identified by APCI using LCMS. As a result, a main peakwas observed at [M+H]+=635.

EXAMPLE 5 1) Synthesis of 4-(6-bromo-pyridin-2-yl)-isoquinoline

4-(6-bromo-pyridin-2-yl)-isoquinoline was synthesized in the same manneras in Example 1-1), except that 2,6-dibromo-pyridin was used instead of3,5-dibromo-pyridin and4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-isoquinoline was usedinstead of 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-quinoline.The 4-(6-bromo-pyridin-2-yl)-isoquinoline was identified by APCI usingLCMS. As a result, a main peak was observed at [M+H]+=285.

2) Synthesis of a Compound Represented by Formula 13

A compound represented by Formula 13 was synthesized in the same manneras in Example 1-2), except that 4-(6-bromo-pyridin-2-yl)-isoquinolinewas used instead of 3-(5-bromo-pyridin-3-yl)-quinoline. The compound ofFormula 13 was identified by APCI using LCMS. As a result, a main peakwas observed at [M+H]+=635.

EXAMPLE 6 1) Synthesis of 3-[5-(4-bromo-phenyl)-pyridin-2-yl]-quinoline

1.0 g (3.51 mmol) of 3-[5-(4-bromo-phenyl)-pyridin-2-yl]-quinoline, 2.8g (14 mmol) of 4-bromophenylboric acid, 0.4 g oftetrakis(triphenylphosphine)palladium(0), 7 ml of 2 M K₂CO₃ and 1.2 g oftetrabutylammoniumbromide were added to a 100 ml round-bottom flask inan argon atmosphere, and 30 ml of THF and 15 ml of toluene were addedthereto. Then, the mixture was refluxed at 100° C. for 12 hours. Whenthe reaction is completed, water was added thereto and the mixture wassubject to extraction using chloroform. Then, an organic layer extractedtherefrom was dried using anhydrous magnesium sulfate and filtered. Asolvent was removed and the resultant was separated using a silica gelcolumn chromatography to obtain 0.54 g of white solid3-[5-(4-bromo-phenyl)-pyridin-2-yl]-quinoline.

2) Synthesis of a Compound Represented by Formula 16

0.5 g (1.38 mmol) of 3-[5-(4-bromo-phenyl)-pyridin-2-yl]-quinoline, 1.0g (1.8 mmol) of2-(9,10-di-naphthalene-2-yl-anthracene-2-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolan,3.6 ml of 1M K₃PO₄ and 20 ml of dioxane were added to a 100 mlround-bottom flask in an argon atmosphere, and the mixture was refluxedat 120° C. for 36 hours. When the reaction is completed, the reactionsolution was cooled to room temperature, and 100 ml of toluene and 100ml of distilled water were added thereto to extract an organic layer.The collected organic layer was dried using MgSO₄ and concentrated. Theresultant was separated using a silica gel chromatography. An elutesolution obtained therefrom was concentrated and dried to obtain 0.67 gof a compound represented by Formula 16 which was identified by APCIusing LCMS. As a result, a main peak was observed at [M+H]+=710.

EXAMPLE 7 Synthesis of a Compound Represented by Formula 30

A compound represented by Formula 30 was synthesized in the same manneras in Example 4-2), except that4,4,5,5-tetramethyl-2-(10-naphthalene-2-yl-anthracene-9-yl)-[1,3,2]dioxaborolanwas used instead of2-(9,10-di-naphthalene-2-yl-anthracene-2-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolan.

EXAMPLE 8 Synthesis of a Compound Represented by Formula 32

A compound represented by Formula 32 was synthesized in the same manneras in Example 3-2), except that4,4,5,5-tetramethyl-2-(10-naphthalene-2-yl-anthracene-9-yl)-[1,3,2]dioxaborolanwas used instead of2-(9,10-di-naphthalene-2-yl-anthracene-2-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolan.The compound of Formula 32 was identified by APCI using LCMS. As aresult, a main peak was observed at [M+H]+=509.

EXAMPLE 9 Synthesis of a Compound Represented by Formula 42

A compound represented by Formula 42 was synthesized in the same manneras in Example 6-2), except that4,4,5,5-tetramethyl-2-(10-naphthalene-2-yl-anthracene-9-yl)-[1,3,2]dioxaborolanwas used instead of2-(9,10-di-naphthalene-2-yl-anthracene-2-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolan.The compound of Formula 42 was identified by APCI using LCMS. As aresult, a main 11 peak was observed at [M+H]+=585.

EXAMPLE 10 Manufacturing and Evaluating Organic Light Emitting Devices

An organic light emitting device having the following structure wasmanufactured using a compound represented by Formula 9 of Example 1 asan electron transport layer, a compound represented by Formula 51 as ahole injection layer, a compound represented by Formula 52 as a holetransport layer, a compound represented by Formula 53 as a host of anemitting layer and a compound represented by Formula 54 as a dopant ofthe emitting layer: ITO/compound of Formula 51(600 Å)/compound ofFormula 52(300 Å)/compound of Formula 53:compound of Formula 54(300Å)/compound of Formula 9(250 Å)/LiF(6 Å)/Al(1500 Å).

A 15 Ω/cm² (1000 Å) ITO glass substrate was cut to a size of 50 mm×50mm×0.7 mm, microwave washed with acetone isopropyl alcohol for 15minutes, microwave washed with pure water for 15 minutes, and washedwith UV ozone for 30 minutes to prepare an anode. The compound ofFormula 51 was vacuum deposited on the substrate to form a holeinjection layer and the compound of Formula 52 was vacuum depositedthereon to form a hole transport layer. Then, the compounds of Formulas53 and 54 were vacuum deposited in a weight ratio of 100:5 to form anemitting layer. Then, the compound of Formula 9 was vacuum deposited onthe emitting layer to form an electron transport layer with a thicknessof 250 Å. LiF was vacuum deposited on the electron transport layer toform an electron injection layer with a thickness of 6 Å, and Al wasvacuum deposited on the electron injection layer to form a cathode witha thickness of 1500 Å. As a result, an organic light emitting deviceillustrated in FIG. 1A was manufactured. The obtained organic lightemitting device had 20 cd/m² of blue light emitting at 6.1 V. Emittingefficiency and brightness half-life at 2000 nit were shown in Table 1.

EXAMPLES 11 TO 18 Manufacturing and Evaluating Organic Light EmittingDevices

Organic light emitting devices were prepared in the same manner as inExample 10, except that compounds synthesized according to Examples 2 to9 were respectively used instead of the compound of Formula 9synthesized according to Example 1 as an electron transport layer.Driving voltage, emitting efficiency and brightness half-life at 2000nit of the organic light emitting device were measured when the organiclight emitting device is driven at a constant current of 20 mA/cm², andthe results are shown in Table 1. In particular, FIG. 3A is a graphillustrating current density-voltage characteristics of the organiclight emitting devices prepared according to Example 12 and ComparativeExample 1, and FIG. 3B is a graph illustrating voltage-brightnesscharacteristics of the organic light emitting devices prepared accordingto Example 12 and Comparative Example 1.

COMPARATIVE EXAMPLE 1 Manufacturing and Evaluating Organic LightEmitting Devices

An organic light emitting device was prepared in the same manner as inExample 10, except that Alq3 was used instead of the compound of Formula9 synthesized according to Example 1 as an electron transport layer.Emitting efficiency, emitting color, brightness and lifetime of theorganic light emitting device were measured, and the results are shownin Table 1. Driving voltage, emitting efficiency and brightnesshalf-life at 2000 nit of the organic light emitting device were measuredwhen the organic light emitting device is driven at a constant currentof 20 mA/cm², and the results are shown in Table 1.

TABLE 1 Brightness Driving Emitting half-life Compound voltage (V)efficiency (cd/A) (hr) Example 10 Example 1 6.1 6.8 1330 Example 11Example 2 5.7 7.2 1280 Example 12 Example 3 5.8 7.3 1400 Example 13Example 4 5.8 7.2 1350 Example 14 Example 5 5.7 7.2 1300 Example 15Example 6 6.2 6.6 1310 Example 16 Example 7 5.6 6.7 1200 Example 17Example 8 5.5 6.7 1220 Example 18 Example 9 5.4 6.9 1290 ComparativeAlq3 6.6 6.7 1240 Example 1

It can be seen that the compound according to an embodiment of thepresent invention has low driving voltage and high emitting efficiencyand has higher electron injecting and transporting capabilities comparedto the compound used as an electron transport layer in ComparativeExample 1. In addition, the organic light emitting devices employing thecompounds of the present invention have excellent lifetimecharacteristics since the compounds of the present invention have highthermal stability due to a high glass transition temperature.

While the present invention has been particularly shown and describedwith reference to exemplary embodiments thereof, it will be understoodby those of ordinary skill in the art that various changes in form anddetails may be made therein without departing from the spirit and scopeof the present invention as defined by the following claims.

1. An anthracene-based compound represented by one of Formula 1 and 2:

wherein R is selected from the group consisting of a hydrogen atom, ahalogen atom, a cyano group, a hydroxyl group, a substituted orunsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20cycloalkyl group, a substituted or unsubstituted C5-C30 heterocycloalkylgroup, a substituted or unsubstituted C1-C20 alkoxy group, a substitutedor unsubstituted C6-C30 aryl group, a substituted or unsubstitutedC6-C30 aralkyl group and a substituted or unsubstituted C2-C30heteroaryl group; L is a bivalent linking group and a substituted orunsubstituted C6-C30 arylene group or a substituted or unsubstitutedC2-C30 heteroarylene group; and m is an integer of 0 to
 3. 2. Theanthracene-based compound of claim 1, wherein the position of theAnthracene connected to the pyridinylquinoline-based group or thepyridinylisoquinoline-based group is one of the positions selected fromthe group consisting of C2, C3, C6, C7, C9 and C10 positions of theanthracene.
 3. The anthracene-based compound of claim 1, represented byone of Formulae 3 to 6 below:

wherein R₁ to R₁₇ are identical to or different from each other and eachindependently one selected from the group consisting of a hydrogen atom,a halogen atom, a cyano group, a hydroxyl group, a substituted orunsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20cycloalkyl group, a substituted or unsubstituted C5-C30 heterocycloalkylgroup, a substituted or unsubstituted C1-C20 alkoxy group, a substitutedor unsubstituted C6-C30 aryl group, a substituted or unsubstitutedC6-C30 aralkyl group and a substituted or unsubstituted C2-C30heteroaryl group; Ar₁, Ar₂ and Ar₃ are identical to or different fromeach other, and Ar₁, Ar₂ and Ar₃ are each independently a substituted orunsubstituted C6-C30 aryl group; L is a bivalent linking group, and L isa substituted or unsubstituted C6-C30 arylene group or a substituted orunsubstituted C2-C30 heteroarylene group; and m is an integer of 0 to 3.4. The anthracene-based compound of claim 3, wherein L is independentlyselected from the groups represented by formulae A1 through A-21:

wherein R′ is identical to or different from each other and one selectedfrom the group consisting of a hydrogen atom, a halogen atom, a cyanogroup, a hydroxyl group, a substituted or unsubstituted C1-C20 alkylgroup, a substituted or unsubstituted C3-C20 cycloalkyl group, asubstituted or unsubstituted C5-C30 heterocycloalkyl group, asubstituted or unsubstituted C1-C20 alkoxy group, a substituted orunsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30aralkyl group and a substituted or unsubstituted C2-C30 heteroarylgroup.
 5. The anthracene-based compound of claim 3, wherein Ar₁, Ar₂ andAr₃ are identical to or different from each other and each independentlyrepresented by one of formulae B1 through B-17:

wherein R′ is identical to or different from each other and one selectedfrom the group consisting of a hydrogen atom, a halogen atom, a cyanogroup, a hydroxyl group, a substituted or unsubstituted C1-C20 alkylgroup, a substituted or unsubstituted C3-C20 cycloalkyl group, asubstituted or unsubstituted C5-C30 heterocycloalkyl group, asubstituted or unsubstituted C1-C20 alkoxy group, a substituted orunsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30aralkyl group and a substituted or unsubstituted C2-C30 heteroarylgroup.
 6. The anthracene-based compound of claim 1, wherein the compoundrepresented by Formula 1 or 2 is one of the compounds represented byFormulae 7 to 50:


7. An anthracene-based compound represented by one of Formulae 3 to 6:

wherein R₁ to R₁₇ are identical to or different from each other and eachindependently one selected from the group consisting of a hydrogen atom,a halogen atom, a cyano group, a hydroxyl group, a substituted orunsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20cycloalkyl group, a substituted or unsubstituted C5-C30 heterocycloalkylgroup, a substituted or unsubstituted C1-C20 alkoxy group, a substitutedor unsubstituted C6-C30 aryl group, a substituted or unsubstitutedC6-C30 aralkyl group and a substituted or unsubstituted C2-C30heteroaryl group; Ar₁, Ar₂ and Ar₃ are each independently selected fromthe group consisting of Formulae B1 through B-17:

L is one of the groups represented by formulae A1 through A-21:

wherein R′ is identical to or different from each other and one selectedfrom the group consisting of a hydrogen atom, a halogen atom, a cyanogroup, a hydroxyl group, a substituted or unsubstituted C1-C20 alkylgroup, a substituted or unsubstituted C3-C20 cycloalkyl group, asubstituted or unsubstituted C5-C30 heterocycloalkyl group, asubstituted or unsubstituted C1-C20 alkoxy group, a substituted orunsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30aralkyl group and a substituted or unsubstituted C2-C30 heteroarylgroup; and m is an integer of 0 to
 3. 8. An organic light emittingdevice comprising a first electrode, a second electrode, and at leastone organic layer between the first electrode and the second electrode,the organic layer comprising the anthracene-based compound of claim 7.9. An organic light emitting device comprising: a first electrode; asecond electrode; and at least one organic layer between the firstelectrode and the second electrode, said at least one organic layercomprising at least one layer comprised of an anthracene-based compoundrepresented by one of Formula 1 and Formula 2:

wherein R is selected from the group consisting of a hydrogen atom, ahalogen atom, a cyano group, a hydroxyl group, a substituted orunsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20cycloalkyl group, a substituted or unsubstituted C5-C30 heterocycloalkylgroup, a substituted or unsubstituted C1-C20 alkoxy group, a substitutedor unsubstituted C6-C30 aryl group, a substituted or unsubstitutedC6-C30 aralkyl group and a substituted or unsubstituted C2-C30heteroaryl group; L is a bivalent linking group and a substituted orunsubstituted C6-C30 arylene group or a substituted or unsubstitutedC2-C30 heteroarylene group; and m is an integer of 0 to
 3. 10. Theorganic light emitting device of claim 9, wherein the at least one layercomprised of the compound represented by one of Formula 1 and Formula 2is one selected from the group consisting of an emitting layer, a holeblocking layer, an electron transport layer and an electron injectionlayer.
 11. The organic light emitting device of claim 9, wherein said atleast one organic layer further comprises at least one layer selectedfrom the group consisting of an emitting layer, a hole injection layer,a hole transport layer, an electron blocking layer, a hole blockinglayer, an electron transport layer and an electron injection layerbetween the first electrode and the second electrode.
 12. The organiclight emitting device of claim 9, wherein the layer comprised of thecompound represented by one of Formula 1 and Formula 2 further comprisesan organic metal complex.
 13. The organic light emitting device of claim9, wherein the layer comprised of the compound represented by one ofFormula 1 and Formula 2 further comprises an ionic salt.
 14. The organiclight emitting device of claim 9, wherein the position of the Anthraceneconnected to the pyridinylquinoline-based group or thepyridinylisoquinoline-based group is one of the positions selected fromthe group consisting of C2, C3, C6, C7, C9 and C10 positions of theanthracene.
 15. The organic light emitting device of claim 9, whereinthe anthracene-based compound is represented by one of Formulae 3 to 6below:

wherein R₁ to R₁₇ are identical to or different from each other and eachindependently one selected from the group consisting of a hydrogen atom,a halogen atom, a cyano group, a hydroxyl group, a substituted orunsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20cycloalkyl group, a substituted or unsubstituted C5-C30 heterocycloalkylgroup, a substituted or unsubstituted C1-C20 alkoxy group, a substitutedor unsubstituted C6-C30 aryl group, a substituted or unsubstitutedC6-C30 aralkyl group and a substituted or unsubstituted C2-C30heteroaryl group; Ar₁, Ar₂ and Ar₃ are identical to or different fromeach other, and Ar₁, Ar₂ and Ar₃ are each independently a substituted orunsubstituted C6-C30 aryl group; L is a bivalent linking group, and L isa substituted or unsubstituted C6-C30 arylene group or a substituted orunsubstituted C2-C30 heteroarylene group; and m is an integer of 0 to 3.16. The organic light emitting device of claim 15, wherein L is one ofthe groups represented by formulae below:

wherein R′ is identical to or different from each other and one selectedfrom the group consisting of a hydrogen atom, a halogen atom, a cyanogroup, a hydroxyl group, a substituted or unsubstituted C1-C20 alkylgroup, a substituted or unsubstituted C3-C20 cycloalkyl group, asubstituted or unsubstituted C5-C30 heterocycloalkyl group, asubstituted or unsubstituted C1-C20 alkoxy group, a substituted orunsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30aralkyl group and a substituted or unsubstituted C2-C30 heteroarylgroup.
 17. The organic light emitting device of claim 15, wherein Ar₁,Ar₂ and Ar₃ are identical to or different from each other and eachindependently represented by one of formulae B-1 through B-17:

wherein R′ is identical to or different from each other and one selectedfrom the group consisting of a hydrogen atom, a halogen atom, a cyanogroup, a hydroxyl group, a substituted or unsubstituted C1-C20 alkylgroup, a substituted or unsubstituted C3-C20 cycloalkyl group, asubstituted or unsubstituted C5-C30 heterocycloalkyl group, asubstituted or unsubstituted C1-C20 alkoxy group, a substituted orunsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30aralkyl group and a substituted or unsubstituted C2-C30 heteroarylgroup.
 18. The organic light emitting device of claim 9, wherein theanthracene-based compound is represented by one of Formula 1 and Formula2 is one of the compounds represented by Formulae 7 to 50: